Process for creaseproofing cellulose-containing fabric with glyoxal-urea-formaldehyde reaction product and a boron compound

ABSTRACT

In combination glyoxal and a boron containing compound selected from the group consisting of the alkali metal borates and boric acid, the combination being incorporable into a resin forming reaction mixture to produce a durable press finish, and an improved process for treating textile fabrics with the same thereby yielding a treated fabric of significantly less discoloration then heretofore known and one exhibiting at the same time, improved strength properties.

United States Patent [191 Readshaw et a1.

[ PROCESS FOR CREASEPROOFING CELLULOSE-CONTAINING FABRIC WITH GLYOXAL-UREA-FORMALDEHYDE REACTION PRODUCT AND A BORON COMPOUND [75] Inventors: Ronald Louis Readshaw, South Charleston; George Henry Lourigan, Charleston, both of W. Va.

[73] Assignee: Union Carbide Corporation, New

York, NY.

[22] Filed: Mar. 4, 1970 [21] Appl. No.: 16,565

52 US. Cl 13mm, 8/1 16.3, 8/133,

3,186,954 6/1965 Hushebeck 8/1 16.3 X 2,876,062 3/1959 Torke et a1. 8/1 16.3 X

FOREIGN PATENTS OR APPLICATIONS 498,763 l/1939 Great Britain 8/ll6.4

[ Oct. 16, 1973 OTHER PUBLICATIONS Crease Resisting Fabrics, J. T. Marsh, 1962, pages 74 and 75, Reinhold Publishing Corp. NYC, N. Y.

An Introduction to Textile Finishing, J. T. Marsh, page 317, 1948, Chapman and Hall, Ltd., London, England.

Merck Index, 7th, Edition, 1960, page 460, Merck & Co., Rahway, N. J.

Primary Examiner-George F. Lesrnes Assistant Examiner-Harold Wolman Attorney-James C. Arvantes, Francis M. Fazio and Aldo J. Coui 7] ABSTRACT In combination glyoxal and a boron containing compound selected from the group consisting of the alkali metal borates and boric acid, the combination being incorporable into a resin forming reaction mixture to produce a durable press finish, and an improved process for treating textile fabrics with the same thereby yielding a treated fabric of significantly less discoloration then heretofore known and one exhibiting at the same time, improved strength properties.

5 Claims, No Drawings PROCESS FOR CREASEPROOFING CELLULOSE-CONTAINING FABRIC WITH GLYOXAL-UREA-FORMALDEHYDE REACTION PRODUCT AND A BORON COMPOUND BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates generally to textile fabrics possessing durable press properties and, more particularly, to cellulose and cellulose-containing textile fabrics treated with novel glyoxal durable press finishes in combination with a boron containing compound, whereby the treated textile fabrics exhibit substantially reduced discoloration and improved strength properties.

2. Description of the Prior Art Crease-resistant finishing agents, i.e., durable press finishes for fibrous material, particularly cellulose and cellulose-containing textile fabrics, have recently become widely used, and a large proportion of such materials now provided to the trade have been treated with such finishes for the production of fabrics having durable press characteristics. Cellulose reactants have been among such agents and one currently used durable press finish comprises the reaction product of glyoxal, urea and formaldehyde in an aqueous medium. While this prior art finish, when applied to a cellulose substrate, does impart certain durable press characteristics, to the treated substrate, e.g., dry wrinkle recovery and durable press qualitites, the latter properties have been sometimes offset by the discoloration of the treated product and by the loss of fabric strength.

In the past, an attempt has been made to employ boron-containing compounds to overcome the discoloration problem (yellowing) of cellulose attendant upon the alkaline degradation of cellulose in the alkaline treatment thereof with sulfone-type cross linking agents. Moreover, while borate compounds have been known to be used as cross linking catalysts for cellulosics, in amounts ranging between about 2 to 4 percent, no color improvement has been achieved therewith. Thus, it would be entirely unexpected that a boroncontaining compound, when used in an acidic media or with acidic catalysts in conjunction with glyoxal based cross linking agents (finishes) applied to cellulosic fabrics, would overcome the prior art problems of discolored and weakened fabrics.

SUMMARY OF THE INVENTION In accord with the invention, it has been discovered that a combination of glyoxal-based durable press finishes, formed by reacting glyoxal, urea and formaldehyde in an aqueous medium, and a boron-containing compound selected from the group consisting of alkali metal borates and boric acid in aqueous medium when applied to a suitable cellulose or cellulose containing textile fabric produces a fabric of significantly less discoloration and of improved strength.

The boron-containing additive may be incorporated into the glyoxal solution per se, in amounts between about 0.5 and about weight percent, preferably between about 6 and about 14 weight percent, and still more preferably, about 9 weight percent; or, it may be added to an aqueous mixture of glyoxal, urea and formaldehyde or, alternatively, the additive may be placed into a suitable pad bath solution for application to the desired fabric. It has been found that the boron additive in the pad bath solution should be in amounts ranging between about 0.01 and about 1.5 weight percent. Maximum reduction of discoloration of the finished treated fabric has been found to be at the level of about 0.5 weight percent boron additive in the pad bath solution. Indeed, amounts below 0.01 percent boron additive and above 1.5 percent boron additive show sharply increased discoloration levels. Thus, the concentration of boron additives is critical.

In terms of fabric content, the boron compound is normally present in amounts ranging between about 0.05 and 1.5 weight percent, based on the weight of fabric, preferably between about 0.125 and about 1.0 weight percent, and still more preferably between about 0.25 and about 0.5 weight percent, using a wet pick-up of 50 to percent.

DESCRIPTION OF THE SPECIFIC EMBODIMENTS In the usual practice of the invention, a durable press resin forming solution is prepared by reacting glyoxal, urea and formaldehyde in any desired sequence, and employing the resultant reaction product 1,3- dimethylol-4,5-dihydroxy-2-imidazolidone in an aqueous medium. This is a typical commercial resin forming solution presently utilized for durable press finished products.

As earlier indicated, an additive comprising a boroncontaining compound selected from the group consisting of alkali metal borates and boric acid may be added either to the glyoxal solution per se or to the glyoxal, urea, formaldehyde reaction mixture in aqueous solution. Illustrative of the boron-containing compounds are the following: boric acid, sodium tetraborate, sodium metaborate, sodium perborate, potassium tetraborate and potassium pentaborate, merely to name a few. Particularly preferred additives on the basis of over-all performance have been found to be sodium tetraborate and sodium metaborate.

Alternatively, the boron additive is incorporated into a standard pad bath solution containing the finish, i.e.,

the glyoxal-based resin forming solution just described; a catalyst, such as zinc nitrate or magnesium chloride; a surfactant, such as Tergitol l5-S--9; a softener, such as Mykon SF; a hand builder such as polyvinyl acetate; and water. The fabric to be treated is passed through the solution for the purpose of wet pickup of the pad solution ingredients and then placed on pin tenter frames. Thereafter, the fabric is usually dried at an elevated temperature to remove the water therefrom. While drying can be accomplished by simply allowing the fabric to remain in contact with air at room temperature, it is preferred to dry the fabric at a temperature of from about 250 to 300F. for a period of about 30 to about seconds, the higher temperatures generally being employed in conjunction'with the shorter drying times.

After this drying step, the fabric is cured by heating at a temperature sufficient to promote the reaction of resin forming solution with the fabric so as to bind it chemically thereto and thereby impart the durable press properties. The curing can be carried out at temperatures from about 300to 360F. for periods ranging from about 30 seconds to 15 minutes, with the higher temperatures generally being employed in conjunction with the shorter heating times. Subjecting the treated textile fabric to a two-step curing procedure involving a pre-curing period and a post-curing period, as hereinbefore described, is preferred, but it is not a critical feature of the process of this invention. lt will be obvious to one skilled in the art that both drying and curing could be accomplished in a single operation or sequential operation.

The term cellulose and cellulose-containing textile fabrics as used throughout the specification and claims is intended to include fabrics, whether woven,

non-woven or knitted, and garments or other articles made from such fabrics. Fabrics containing cellulose, regenerated cellulose, and mixtures of the two are intended to be within the scope of the present invention. illustrative of the textile fabrics to which this invention relates are cotton fabrics, linen fabrics, rayon fabrics, fabrics consisting of blends of cotton, linen or rayon fibers, and fabrics consisting of blends of cellulosic fibers and non-cellulosic fibers, such as, for example, polyester or polyamide fibers.

Thus, by subjecting any one of the above listed fabrics to a textile treating solution containing the glyoxal based resin forming mixture and the boron containing compound, it has been found that textile fabrics are obtainable, which exhibit substantial reduction in discoloration of the treated fabric, a stronger fabric and, as an incidental feature, reduction in shade change. As indicated, the amount of boron-containing additive is in the range between about 0.01 and about 1.5 weightpercent of the pad bath treating solution. Maximum reduction of discoloration of the finished treated product has been found to be at the level of about 0.5 weight percent additive.

Evaluation of the textile fabrics subjected to the process of this invention was made in accordance with accepted test procedures of the ASTM (American Society For Testing Materials), or the AATCC (American Association of Textile Chemists and Colorists), or by procedures that are fully described herein. The following tests were conducted:

Dry Wrinkle Recovery- AATCC Tentative Test Method 66-19591 Tensile Strength -ASTM Method 13-1682 (Grab) Tear Strength ASTM Method D-1424-59 (Elmendorf) Damage Caused by -AATCC Tentative Test Method. 114-1967 Retained Chlorine Durable Press Rating AATCC Test Method- 124 Yellowness lndex Measured with a Hunterlab Model D-40 reflectometer excluding filter GreemBlue Reflectance Yellowness Increasingly positive numbers indicate increasingly yellow fabric The following definitions will also be applicable in the Examples and wherever appearing in the specification:

Catalyst X-4 An acetic 5638615685 of z nitrate hexahydrate.

Mykon SF A nonionic paraffin-free polyethylene emulsion press finish and marketing the finish containing the additive, whence it will be eventually added to the pad bath solution. In yet another alternative method of introducing the boron salt to a durable press treating bath, the boron salt is added to a raw material, e.g., glyoxal, that is used to make a durable press finish. In other words, sodium metaborate can be added to glyoxal, the glyoxal used to make'a durable press finish and the finish used to treat the fabric to impart durable press properties thereto. The various alternative methods of introducing the boron containing additive will be better understood in conjunction with the following specific examples. l-7.

Example 1 The pH of a mixture of 170 grams of 40 percent glyoxal (1.17 rnoles) and 187.6 grams of 37.5 percent unhibited formaldehyde (2.34 moles) was adjusted to 5.5 with 7.4 grams of a 30 percent aqueous sodium acetate solution; 70.4 grams of urea (1.17 moles) was then added and the pH of the mixture raised to 7.0 with 1.3 grams of a 10 percent aqueous sodium hydroxide solution and maintained at this pH for the remainder of the reaction with the periodic addition of 14.8 grams of the 10 percent aqueous sodium hydroxide solution. The temperature of the reaction mixture was raised to 60C. and maintained at this temperature for 1% hours. The reaction product, l,3-dimethylol-4,5-dihydroxy-2- imidazolidone, was cooled to room temperature and 24.0 grams of distilled water was added to make a 45 percent solutio n. The formaldehyde content of the 45 percent productwasbfi percent, and til- 17.0 and the color (Pt), ASTM Dl209 -62.

Example 2 The pH of a mixture of grams of 40 percent glyoxal (1.17 moles) and 187.6 grams of 37.5 percent uninhibited form-aldehyde (2.34 moles) was adjusted to 5.5 with 7.6 grams of a 30 percent aqueous sodium acetate solution; 70.4 grams of urea (1.17 moles) was then added and the pH of the mixture raised to 7.0 with 1.3 grams of a 10 percent aqueous sodium hydroxide solution. Six and one-half grams of sodium tetraborate was added intermittently with 13.3 grams of 24 percent sodium hydroxide. The intermittent addition of base is necessary to maintain the pl-l of the reaction mixture between 6.0 and 7.0. After the sodium tetraborate had been added, the temperatureof the reaction was raised to 60C. and the pH maintained at 7.0 for 2 hours, after which another 6.5 grams of sodium tetraborate was added. The pi-l of the reaction was maintained at 7.0 during and after the reaction period by the addition of 31.8 grams of 10 percent sodium hydroxide. The formaldehyde content of the reaction product was nil, the color 65 (Pt) and the pH 7.0.

Example 3 The procedure used to make the finish of this example was the same as that used to make the finish of Example 2 with the exception of boric acid being used instead of sodium tetraborate. The formaldehyde content of the present finish was nil, the color 60 (Pt) and the pH 7.0.

Example 4 T sp of mix of 1 srssssffii) ns sri 6 glyoxal (1.17 moles) and 187.6 grams of 37.5 percent percent glyoxal (1.17 moles) and 187.6 grams of 37.5 uninhibited formaldehyde (2.34 moles) was adjusted to percent uninhibited formaldehyde (2.34 moles) was 5.5 with 7.3 grams ofa 30 percent aqueous sodium aceadjusted to 5.5 with 6.8 grams ofa 30 percent aqueous tate solution; 70.4 grams of urea 1.17 moles) was then sodium acetate solution; 70.4 grams of urea (1.17 added and the pH of the mixture raised to 7.0 with 1.3 5 moles) was then added and the pH of the mixture grams of a percent aqueous sodium hydroxide soluraised to 7.0 with 1.2 grams of a 10 percent aqueous sotion and maintained at this pH for the remainder of the dium hydroxide solution and maintained at this pH for reaction with the periodic addition of 14.8 grams of the the remainder of the reaction with the periodic addi- 10 percent aqueous sodium hydroxide solution. The tion of 14.4 grams of the 10 percent aqueous sodium temperature of the reaction mixture was raised to 60C. 10 hydroxide solution, The temperature of the reaction and maintained at this temperature for 2 hours. The remixture was raised to 60C and maintained at this temaction product, l,3-dimethyl0l-4,5-dihydr0Xy-2- perature for 2 hours. The reaction product 1,3- imidazolidone, was cooled to room temperature and dimethylol-4,5-dihydroxy-Z-imidazolidone, was cooled enough distilled water was added to make a 45 percent t ro m temperature and enough distilled water was solution. The formaldehyde content of the 45 percent 5 dd d to m ke a 45 percent solution. The formaldeproduct was 0.30 percent, the pH 7.0 and the color 65 h d content f h 45 percent product was 030 U- cent, the pH 7.0 and the color 90 (Pt).

Example 5 Example 7 To 170 grams of 40 percent glyoxal (Union Carbide Corporation) was added 15 grams of sodium metabor- The procedure used to make the finish of Example 6 ate. The mixture remained at ambient temperature was the same used to make the finish of the present ex- (24C.) for 3 days and was then used in the following ample with the exception that 15.0 grams of sodium manner to make a glyoxal-based finish. The pH of a metaborate had three days previously been added to mixture of 170 grams of 40 percent glyoxal (1.17 170.0 grams of Nobel Bozel glyoxal and this material moles), to which had been added 15 grams of sodium was used to make the present finish. The formaldehyde metaborate and 187.6 grams of 37.5 percent uninhibcontent of the finish was 0.2, the color 70 (Pt) and the ited formaldehyde (2.34 moles) was adjusted to 5.5 pH 7.0. with 5.3 grams of a percent aqueous sodium acetate Each of the finishes made by the procedures of 1 solution; 70.4 grams of urea (1.17 moles) was then 30 through 7 were then individually applied to white cotadded and the pH of the mixture raised to 7.0 with 1.0 ton 136 X 64 broadcloth which had been desized, gram of a 10 percent aqueous sodi urnhydroxide solu scoured, bleached and mercerized by padding through tion and maintained at this pH for the remainder of the a laboratory padder at a wet pick-up of 75 percent. The reaction with the periodic addition of 12.2 grams of the fabrics were placed on pin tenter frames, dried at 10 percent aqueous sodium hydroxide solution. The 300F. for 1.5 minutes and cured for 1.5 minutes at temperature of the reaction mixture was raised to 60 340F. or 15 minutes at 320F. in a laboratory oven. C. and maintained at this temperature for 1% hours. Table 1 constituting Examples 8 to 14 lists the treat The reaction product, l,3-dimethyl-4,5-dihydroxy-2- ing or pad bath formulations.

imidazolidone, was cooled to room temperature and Tables 11 and Ill detail the fabric performance propenough distilled water was added to make a 45 percent erties shown by fabrics treated by the bath formulations solution. The formaldehyde content of the percent illustrated by Examples 8 to 14 respectively. In Tables product was 0.20 percent, the pH 7.0 and the color 45 11 and 111, the series denoted by Examples 80, 9a, 10a (Pt). show the effect of adding the sodium tetraborate or In order to illustrate that this invention is applicable boric acid to the reaction of glyoxal, urea and formalto other commercially available glyoxal material, the dehyde to make the glyoxal-based finish used to impart finishes of Examples 6 and 7 were prepared using durable press properties to the fabrics. The series de- Nobel Bozel glyoxal, another commercially available noted by Examples 11a, 12a, 13a and 14a show that soglyoxal. dium metaborate can be added to glyoxal which is subsequently used to make a glyoxal-based durable press Example 6 fiaisirsaa Sim yields the aesrea-rnsratneaa mas MP1?.PHPQQEKFPEBZ1Z9EBHiQffiQEfiQZPlfiQ g t btliPstfsin Properties- TABLE I.TREATMENT BATH FORMULATION Composition, percent by weight Ingredients Additive Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 Ex. 13 Ex. 14

Durable press finish None 17. 8

Do Sodium tetraborate 17.8

Do Boric acid 17.8

Do None Do Sodium metaborate .Catalyst X4 (mod. zinc nitrate, Sun Chem. Co.) Mykon SF (polyethylene softener, Sun Chem. Co.) Tergitol 15-S-9 (nonionic surfactant, U.C.C.) Distilled water TABLE IL-FABRIC PERFORMANC'EPROPERTIES 'AT A CURE OF 1.5 MINUTES A-r'w F.

Treatment Property Ex. 8a Ex. 9a Ex. a Ex. 11a Ex. 12a Ex. 13a Ex. 14a

Yellowness index t 067 026 03D 036 03 032 Tear strength (we lfill) grams 400/208 704/464 672/448 560/352 592/400 528/352 608/416 Tensile strength pounds 19 26 Dry wrinkle recovery (wa -fill) Durable press rating turnb e dry/spin dry Damage caused by retained chlorine, percent loss in st TABLE IIL-FABRIC PERFORMANCE PROPERTIES AT A CURE TIME OF 15 MINUTES AT 320 F.

Treatment Property Ex. 8a Ex. 9:; Ex. 10a Ex. 11a Ex. 12a Ex. 13a Ex. 14

Yellowness index 124 067 066 074 048 Tear strength (Warp/fill) gra 320/128 640/416 576/368 416/288 512/352 352/272 512/352 Tensile strength (fill) pounds, 22 24 Dry wrinkle recovery (warp-fill) deg 296 293 292 Durable press rating tumble dry/spin dry. 3.7/3.3 3. 4/32 3. 4/3. 1

Damage caused by retained chlorine, percent loss in strength 4. t N

A convenient method for introducing the boron salts is to add them directly to the treating bath. However, no loss in efficiency was noted when the salt was added either to the durable press finish or to the glyoxal or to the other of the raw materials used to make the durable press finish, i.e., urea or formaldehyde.

Effect of Boric Acid Salts on Fabric Discoloration and Fabric Strength TABLE IV.TREATING BATH FORMULATION Composition, percent by Weight Ex. Ex Ex. Ex. Ex Ex. Ex. Ex.- Ex. Ex. Ex Ex Ingredients 15 16 17 8 19 20 21 22 23 24 25 26 Durable press finish (Permafresh 183, Sun Chemical Company) .8 .8 Modified zinc nitrate catalyst (Catalyst X-4, Sun Chemical Compan .2 .2 Polyethylene softener (Mykon SF, Sun Chemical Company) .8 .8 N anionic surfactant (Tergitol 15S9, Union Carbide Corp). .1 1

Sodium tetraborate. Sodium metaborate. Sodium perborate Potassium tetraborate Potassium pentaborate Ammonium biborate Ammonium pentsborate" Boric acid Distilled Watetz Durable press finish (Aerotex 101, American Cyanamid Company) TABLE V.-FABRIC PERFORMANCE PROPERTIES Examples Property 15a 16a 17a 18a 19a 20a 21a 22a. 23a 24a 26a 26a Yellowness index 134 080 0S4 083 069 069 075 O78 148 135 041 032 Tear strength warp/fill (gram 384/256 496/336 432/272 416/288 512/336 496/320 480/352 448/320 384/ 288 368/240 608/415 656/454 Dry wrinkle recovery (degrees) 297 285 289 288 277 284 280 285 283 280 280 258 Nora-The curing temperature for Examples 25a and 25a was 320 F.

in accord with the invention, the presence of certain boric-acid saltsin treating baths, containing commer:

'cial glyoxal-based durable press finishes, beneficially reduces fabric discoloration that is normally associated 55 with this type of fabric treatment. They also significantly improve the fabric strength properties.

White cotton 136 X 64 broadcloth desized, scoured, bleached and mercerized was padded with the treating baths detailed in Table IV, and identified as Examples 0 With the exception of the treatments containing the ammonium borates, the difference in each series between the control treatment and the treatments containing boron salts show the significant decrease in fabric discoloration and the increase in fabric strength that are effected by the presence of boron-containing materials. On the basis of over-all performance, sodium tetraborate and sodium metaborate are to be preferred. Although there is a slight decrease in durable press properties '(dry wrinkle recovery), this deficiency can be overcome by altering the composition of the treating bath as will be seen subsequently. Effect of Concentration of Sodium Tetraborate and Sodium Metaborate on Fabric Discoloration and Fabric Strength The degree of improvement in fabric discoloration and fabric strength is effected by the concentration o f sodium tetraborate or sodium metaborate in the treating bath. Following are examples which show the degree by which discoloration and strength are effected.

White cotton broadcloth desized, scoured, bleached and mercerized was padded (Examples 27 through 36; summarized in Table VI) through a laboratory padder at a wet pick-up of 75 percent. The fabrics were then placed on pin tenter frames, dried at 300F. for 1.5 minutes and cured to 1.5 and 15.0 minutes at 340-F. in a laboratory oven. Permafresh" 183 was the commercial glyoxal-based durable press finish used in these experiments.

The first series, Examples 27a-31a, showed the effect of the concentration of sodium tetraborate. The second series, Examples 32a-36a, showed the effects of sodium metaborate concentration. Fabric performance properties are summarized in Tables VII and VIII below.

colora ion ohta nedt. 1 Effect of Catalyst Concentration On The Fabric Performance Properties of Fabric Treated With A Glyoxal- Based Durable Press Finish In The Presence of Sodium Tetraborate White cotton broadcloth desized, scoured, bleached- TABLE-VL-TREATING BATH FORMULATION Compositions, percent by weight Ex. Ex. Ex. Ex. -Ex. Ex. Ex. Ex. Ex. Ex. Ingredients 2?- 28 29 30 31 32 33 34 35 36 Durable press finish (Permairesh 183, Sun Chemical Company) 17. 8 17. 8 17. 8 17. 8 17. 8 17.8 17 8 17. 8 17. 8 17.8 Modified zinc nitrate catalyst (Catalyst X-4, Sun Chemical Com 2 3. 2 3. 2 3. 2 3. 2 3. 2 3 2 3. 2 3. 2 3. 2 Polyethylene softener (Mykon SF, Sun Chemical Company) .8 1. 8 1. 8 1.8 1. 8 1. 8 1 8 1. 8 1. 8 1. 8 Nonionic surfactant (Tergitol -5-9, Union Carbide Corp.) 1 0.1 O. 1 0. 1 0. 1 0. 1 0 1 0.1 0. 1 0. 1 Sodium tetraborate 0. 0. 50 0.75 1. 00 Sodium metaborate" 0. 25 0. 50 0. 75 1. 00 76. 85 76. 6 76. 35 76. 1 77 1 76. 85 76. 6 76. 35 76. 1

TABLE VIL-FABRIC PERFORMANCE PROPERTIES AT A CURE TIME OF 1.5 MINUTES AT 300 F.

Treatment Property Ex. 27a Ex. 28a Ex. 29a Ex. a Ex. 31a Ex. 32a Ex. 33a Ex. 34a Ex. a Ex. 36a

Yellowness index 040 036 041 035 .044 043 049 036 039 040 Tearstrength (warp/fill) grams 560/368 576/416 688/480 816/544 864/624 560/345 650/460 740/500 805/570 895/705 Tens11e strength (fill) pounds 20 25 27 32 19 22 25 28 31 Dry wrinkle recoyery (warp-fill) degrees-.. 293 286 274 269 239 295 282 283 260 4 244 Durable press rating (tumble dry/spin dry) 3. 6/3. 3 3. 4/3.1 3. 2/2. 8 3. 1/2. 3 2. 7/2. 2 3. 6/3. 2 3. 4/3. 1 3. 4/3. 1 3. 1/2. 9 3. 1/2. 5 Damage caused by retained chlorine (percent loss in strength) Nil Nil 6. 7 4. 1 N11 N11 4. 5 2. 8 6. 5 9. 0

TABLE VIII.FABRIC PERFORMANCE PROPERTIES AT A CURE TIME OF 15 MINUTES AT 340 F.

Treatment Property Ex. 27a Ex. 28a Ex. 2119. Ex. 3021 Ex. 31a Ex. 32a Ex. 33a Ex. 34a- Ex. 35a Ex. 36a

Yellowness index .135 099 076 092 099 012 075 071 077 084 Tear strength (warp/fill) grams- 432/272 448/304 544/336 656/400 672/432 580/315 505/256 630/363 630/425 752/452 Tensile strength (fill pounds 16 18 20 22 25 19 17 21 22 25 Dry wrinkle recovery (warp-fill) degrees 284 292 280 273 266 4 296 291 285 289 274 Durable press rating, tumb e dry/spin dry 3. 6/3. 3 3. 5/3. 2 3. 5/3. 2 3. 4/3. 1 3.4/3.0 3.5/3. 2 3. 4/3. 2 3. 4/3. 2 3.4/3. 1 3. 1/3.0 Damage caused by retained chlorine, percent loss in strength Nil 2. 9 5.0 2. 5 Nil Nil 4. 8 9. 8 N11 Ni Although the higher the concentration of the sodium TABLE IX borates in the treating bath the higher the strength TREATING T FORMULATION properties of the fabric, the optimum concentration in EXAMPLES relation to fabric discoloration is 0.5 weight percent. At D A" d w 8 g isti e ater .8 P intteeewhimuusitm amqn taifmnqg s; .m ..1 1. 181 1 1.8 11.11 11.8 11.8

Dry wrinkle recovery (warp-fill) degre Tergitol lS-S-Q 0.l 0.! 0.l 0.1 Mykon SF L8 L8 1.8 1.8 Sodium Tetraborate 0.5 0.5 0.5 0.5 Modified Zinc Nitrate Catalyst (catalyst X-4) 3.0 4.0

12 said solution also containing formaldehyde and in the proportions of l mole of glyoxal to 2 moles of formaldehyde, adjusting the pH of said solution to pH 5.5,

prior to forming said reaction product, and then adding TABLE X.FABRIC PERFORMANCE PROPERTIES AT A CURE TIME OF 1.5 MINUTES AT 340 F.

Property Yellowness index Tear strength (warp/fill) grams. Tensile strength (fill) pounds Dry wrinkle recovery (warp-fill) degrees.-. Durable press rating tumble dry/spin dry Damage caused by retained chlorine, percent loss in strength Treatment Ex. 37a Ex. 38a Ex. 39a Ex. 40a

3. Nil 12. 5 Ni TABLE XI.FABRIC PERFORMANCE PROPERTIES AT A CURE TIME OF MINUTES AT 340 F.

Treatment- Property Ex. 37a Ex. 38a Ex. 3% Ex. 40a

Yellowness index 067 053 059 130 Tear strength (warp/fill) grams. 672/432 608/464 544/384 480/336 Tensile strength (fill) pounds 27 26 23 19 Durable press rating tumble dry/spin dry Damage caused by retained chlorine, perce 280 zao 290 294 a. 2 2. 9 a. 3 2. 9 3. 4 3. 0 a. 3 3. 2 Nil 3. 7 1. 0 N11 The use of the boron salts slightly effects the effectiveness of the catalyst. The slight loss in catalyst effidium metaborate to an aqueous solution of glyoxal,-

proportionately 1 mole of urea to said solution and changing the pH of the solution of pl-l7 which is maintained during the formation of said reaction product, said sodium metaborate being added to said glyoxal in an amount ranging between about 0.5 and 20 weight percent based on the weight of the total solution.

2. The process of claim 1 wherein said sodium metaborate is added in an amount ranging between about 6 and 14 weight percent.

3. A process according to claim 1 wherein said textile fabric is a blend of polyester and cotton.

4. A process according to claim 1 wherein said textile fabric is cotton.

5. A process according to claim 1 wherein said textile fabric is rayon. 

2. The process of claim 1 wherein said sodium metaborate is added in an amount ranging between about 6 and 14 weight percent.
 3. A process according to claim 1 wherein said textile fabric is a blend of polyester and cotton.
 4. A process according to claim 1 wherein said textile fabric is cotton.
 5. A process according to claim 1 wherein said textile fabric is rayon. 